HD lifters should be changed every 25K. Many get by with more miles. I know several that did not. Even S&S recommends this interval.
There is no requirement or suggestion to "pump up" lifters prior to installing.

 

For the record there IS a difference in adjusting pushrods with lifters that are pumped up as opposed to dry. with pumped up lifters you have to adjust the pushrods on one cylinder then wait usually 10-15 min for them to bleed down to where you can spin the pushrod by hand, then rotate engine to low lobe on rear and repeat. with dry lifters theres no waiting for the lifter to bleed down. you adjust then spin and repeat.

When i install new lifters i just coat them with oil, insert them, pour a little oil in from the top, then adjust pushrods. once everything is done and buttoned back up remove spark plugs and crank engine over for about 15 sec a couple times. then start the bike and let idle for several minutes. then cut the bike off, and wait about 10 min. Restart and after about a minute they will be pumped up.

Whatever you do, dont listen to the H-D service manual. It states that the lifters can take a "few miles of riding" to pump up. i dont know about you but im not going to ride a bike and run it through the gears with dry lifters.

 

Your doing right.

I put in S&S travel limiters.

After doing that not a lot of, "pumping", you can do.

S&S says to do what you said, get a lot of oil onto everything and take it very easy for a little while, after adjusting. I just puttered around the street a little, idleing really.
They come on up in a couple minutes.

 

Really? Change the lifters every 25k miles? That seems a bit ridiculous, they should last longer than that.